AU594654B2 - 1,2 dialkoxy-omega-trialkylammonium cationic surfactants - Google Patents

1,2 dialkoxy-omega-trialkylammonium cationic surfactants Download PDF

Info

Publication number
AU594654B2
AU594654B2 AU51853/86A AU5185386A AU594654B2 AU 594654 B2 AU594654 B2 AU 594654B2 AU 51853/86 A AU51853/86 A AU 51853/86A AU 5185386 A AU5185386 A AU 5185386A AU 594654 B2 AU594654 B2 AU 594654B2
Authority
AU
Australia
Prior art keywords
compound
formula
alkyl
carbon atoms
same
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
AU51853/86A
Other languages
English (en)
Other versions
AU5185386A (en
Inventor
Deborah A. Eppstein
Philip L. Felgner
Gordon H. Jones
Richard B. Roman
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Syntex USA LLC
Original Assignee
Syntex USA LLC
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Syntex USA LLC filed Critical Syntex USA LLC
Publication of AU5185386A publication Critical patent/AU5185386A/en
Application granted granted Critical
Publication of AU594654B2 publication Critical patent/AU594654B2/en
Anticipated expiration legal-status Critical
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
    • C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
    • A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
    • A61K47/186—Quaternary ammonium compounds, e.g. benzalkonium chloride or cetrimide
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • A61K9/127—Liposomes
    • A61K9/1271—Non-conventional liposomes, e.g. PEGylated liposomes, liposomes coated with polymers
    • A61K9/1272—Non-conventional liposomes, e.g. PEGylated liposomes, liposomes coated with polymers with substantial amounts of non-phosphatidyl, i.e. non-acylglycerophosphate, surfactants as bilayer-forming substances, e.g. cationic lipids
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N15/00—Mutation or genetic engineering; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification; Use of hosts therefor
    • C12N15/09—Recombinant DNA-technology
    • C12N15/87—Introduction of foreign genetic material using processes not otherwise provided for, e.g. co-transformation
    • C12N15/88—Introduction of foreign genetic material using processes not otherwise provided for, e.g. co-transformation using microencapsulation, e.g. using amphiphile liposome vesicle

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Genetics & Genomics (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Biomedical Technology (AREA)
  • Wood Science & Technology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Zoology (AREA)
  • Molecular Biology (AREA)
  • General Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • Biophysics (AREA)
  • Dermatology (AREA)
  • Plant Pathology (AREA)
  • Dispersion Chemistry (AREA)
  • Microbiology (AREA)
  • Biochemistry (AREA)
  • Physics & Mathematics (AREA)
  • Medicinal Preparation (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Detergent Compositions (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pyrrole Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Developing Agents For Electrophotography (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
AU51853/86A 1985-01-07 1986-01-06 1,2 dialkoxy-omega-trialkylammonium cationic surfactants Expired AU594654B2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US68940785A 1985-01-07 1985-01-07
US689407 1991-04-22

Publications (2)

Publication Number Publication Date
AU5185386A AU5185386A (en) 1986-07-17
AU594654B2 true AU594654B2 (en) 1990-03-15

Family

ID=24768317

Family Applications (1)

Application Number Title Priority Date Filing Date
AU51853/86A Expired AU594654B2 (en) 1985-01-07 1986-01-06 1,2 dialkoxy-omega-trialkylammonium cationic surfactants

Country Status (8)

Country Link
EP (1) EP0187702B1 (de)
JP (2) JPH0662517B2 (de)
AT (1) ATE50983T1 (de)
AU (1) AU594654B2 (de)
CA (1) CA1288774C (de)
DE (1) DE3669503D1 (de)
NZ (1) NZ214716A (de)
ZA (1) ZA8681B (de)

Families Citing this family (58)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4897355A (en) * 1985-01-07 1990-01-30 Syntex (U.S.A.) Inc. N[ω,(ω-1)-dialkyloxy]- and N-[ω,(ω-1)-dialkenyloxy]-alk-1-yl-N,N,N-tetrasubstituted ammonium lipids and uses therefor
SE464448B (sv) * 1985-04-04 1991-04-29 Int Genetic Sciences Fusogen fosfolipidvesikel innehaallande ett kvaternaert ammoniumhydroxidsalt i membranet samt ett foerfarande foer dess framstaellning
US5320906A (en) * 1986-12-15 1994-06-14 Vestar, Inc. Delivery vehicles with amphiphile-associated active ingredient
US6214804B1 (en) 1989-03-21 2001-04-10 Vical Incorporated Induction of a protective immune response in a mammal by injecting a DNA sequence
US5703055A (en) * 1989-03-21 1997-12-30 Wisconsin Alumni Research Foundation Generation of antibodies through lipid mediated DNA delivery
US5693622A (en) * 1989-03-21 1997-12-02 Vical Incorporated Expression of exogenous polynucleotide sequences cardiac muscle of a mammal
US6867195B1 (en) 1989-03-21 2005-03-15 Vical Incorporated Lipid-mediated polynucleotide administration to reduce likelihood of subject's becoming infected
US6673776B1 (en) 1989-03-21 2004-01-06 Vical Incorporated Expression of exogenous polynucleotide sequences in a vertebrate, mammal, fish, bird or human
US6706694B1 (en) 1990-03-21 2004-03-16 Vical Incorporated Expression of exogenous polynucleotide sequences in a vertebrate
US6228844B1 (en) 1991-11-12 2001-05-08 Vical Incorporated Stimulating vascular growth by administration of DNA sequences encoding VEGF
US5264618A (en) * 1990-04-19 1993-11-23 Vical, Inc. Cationic lipids for intracellular delivery of biologically active molecules
DE4013632A1 (de) * 1990-04-27 1991-10-31 Max Planck Gesellschaft Liposomen mit positiver ueberschussladung
ES2089226T3 (es) * 1990-09-06 1996-10-01 Johnson & Son Inc S C Procedimiento para estabilizar liposomas y composiciones que los contienen.
GB2250998A (en) * 1990-12-21 1992-06-24 Unilever Plc Cosmetic cleansing composition
WO1993020038A1 (en) * 1992-04-03 1993-10-14 Gist-Brocades N.V. Selective n-acylation of amino alcohols
US5674908A (en) 1993-12-20 1997-10-07 Life Technologies, Inc. Highly packed polycationic ammonium, sulfonium and phosphonium lipids
US6995008B1 (en) 1994-03-07 2006-02-07 Merck & Co., Inc. Coordinate in vivo gene expression
JPH07308570A (ja) * 1994-05-16 1995-11-28 Hirotaka Hirata 界面活性物質を含む分子複合体
WO1997019675A2 (en) * 1995-11-30 1997-06-05 Vical Incorporated Complex cationic lipids
DE19605175A1 (de) 1996-02-13 1997-08-14 Sourovoi Andrej Dr Lipidverbindungen und deren Verwendung
ES2187812T3 (es) 1996-09-13 2003-06-16 Lipoxen Technologies Ltd Composicion de liposomas.
US7384923B2 (en) 1999-05-14 2008-06-10 Lipoxen Technologies Limited Liposomes
US6686339B1 (en) 1998-08-20 2004-02-03 Aventis Pasteur Limited Nucleic acid molecules encoding inclusion membrane protein C of Chlamydia
EP1105490A1 (de) 1998-08-20 2001-06-13 Aventis Pasteur Limited Einschlussmembranprotein c von chlamydia kodierende nukleinsäuremoleküle
US6693087B1 (en) 1998-08-20 2004-02-17 Aventis Pasteur Limited Nucleic acid molecules encoding POMP91A protein of Chlamydia
PT1129064E (pt) 1998-11-12 2008-01-31 Invitrogen Corp Reagentes de transfecção
CA2721011A1 (en) 1999-10-22 2001-05-03 Aventis Pasteur Limited Modified gp100 and uses thereof
EP1792995A3 (de) 2000-05-08 2007-06-13 Sanofi Pasteur Limited Chlamydia Antigene, entsprechende DNS Fragmente und ihre Verwendungen
WO2001085932A2 (en) 2000-05-10 2001-11-15 Aventis Pasteur Limited Immunogenic polypeptides encoded by mage minigenes and uses thereof
EP1356820A1 (de) 2002-04-26 2003-10-29 Institut National De La Sante Et De La Recherche Medicale (Inserm) DNA-Impfstoff kombiniert mit einen Apoptoneauslöser von Tumorzellen
JP2006273341A (ja) * 2005-03-28 2006-10-12 Toppan Printing Co Ltd 乾燥能力インジケーター機能付蓋
JP5072275B2 (ja) 2006-07-03 2012-11-14 テルモ株式会社 閉鎖小胞の分離方法、製剤の製造方法および評価方法
RU2459631C2 (ru) 2006-10-06 2012-08-27 Дзе Скриппс Рисерч Инститьют Композиция днк для вызова иммунного ответа против опухолеассоциированных макрофагов
JP5080779B2 (ja) 2006-10-25 2012-11-21 テルモ株式会社 リポソーム製剤の製造方法
WO2009129387A2 (en) * 2008-04-16 2009-10-22 Abbott Laboratories Cationic lipids and uses thereof
WO2010109016A1 (en) 2009-03-27 2010-09-30 Institut National De La Sante Et De La Recherche Medicale (Inserm) Kanamycin antisense nucleic acid for the treatment of cancer
WO2011064790A1 (en) * 2009-11-30 2011-06-03 Avra Laboratories Pvt. Ltd A novel process for making aliskiren, its novel intermediates and certain novel compounds
SG10201407996PA (en) 2009-12-23 2015-01-29 Novartis Ag Lipids, lipid compositions, and methods of using them
WO2011113160A1 (en) 2010-03-17 2011-09-22 Socpra - Sciences Et Génie, S.E.C. Bacterial vaccine components from staphylococcus aureus and uses thereof
CN102884041B (zh) 2010-04-28 2015-04-15 协和发酵麒麟株式会社 阳离子性脂质
JP5902617B2 (ja) 2010-04-28 2016-04-13 協和発酵キリン株式会社 カチオン性脂質
CA2798837A1 (en) 2010-06-07 2011-12-15 Pfizer Inc. Her-2 peptides and vaccines
JP2013095755A (ja) 2011-11-02 2013-05-20 Kyowa Hakko Kirin Co Ltd カチオン性脂質
CN104159615B (zh) 2011-12-12 2017-08-18 协和发酵麒麟株式会社 含有阳离子性脂质的组合的脂质纳米粒子
JP6182457B2 (ja) 2011-12-12 2017-08-16 協和発酵キリン株式会社 カチオン性脂質を含有するドラックデリバリーシステムのための脂質ナノ粒子
MX359257B (es) 2012-05-04 2018-09-19 Pfizer Antígenos asociados a próstata y regímenes de inmunoterapia basados en vacuna.
CA2878314A1 (en) 2012-07-16 2014-01-23 Kyowa Hakko Kirin Co., Ltd. Rnai pharmaceutical composition for suppressing expression of kras gene
WO2016011203A1 (en) 2014-07-15 2016-01-21 Life Technologies Corporation Compositions with lipid aggregates and methods for efficient delivery of molecules to cells
EP3169309B1 (de) 2014-07-16 2023-05-10 Novartis AG Verfahren zur verkapselung einer nukleinsäure in einem lipidnanopartikelhost
WO2017066643A1 (en) 2015-10-14 2017-04-20 Bio-Path Holding, Inc. P-ethoxy nucleic acids for liposomal formulation
US10525138B2 (en) 2015-12-25 2020-01-07 Kyowa Hakko Kirin Co., Ltd. Compound as cationic lipid
JP6820935B2 (ja) 2016-01-19 2021-01-27 ファイザー・インク がんワクチン
WO2018072031A1 (en) 2016-10-21 2018-04-26 Socpra Sciences Et Génies S.E.C. Vaccine constructs and uses thereof against staphylococcus infections
US11339209B2 (en) 2016-11-14 2022-05-24 Novartis Ag Compositions, methods, and therapeutic uses related to fusogenic protein minion
IT201900007060A1 (it) 2019-05-21 2020-11-21 St Superiore Di Sanita Cellule tumorali ingegnerizzate e loro usi
IT201900012540A1 (it) 2019-07-22 2021-01-22 Humanitas Mirasole Spa Inibitori di CHI3L1 e loro usi
US20220185852A1 (en) 2020-12-11 2022-06-16 Bayer Animal Health Gmbh Methods and compositions for improved production of an antigen for use in an s. aureus vaccine
WO2024200831A1 (en) 2023-03-30 2024-10-03 Vivadju Pvax14 nucleic acid in combination with all-trans retinoic acid (atra) and a checkpoint inhibitor for the treatment of cancer

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3567729A (en) * 1968-01-12 1971-03-02 Swift & Co Diquaternary ammonium halides

Also Published As

Publication number Publication date
JPH0662517B2 (ja) 1994-08-17
EP0187702B1 (de) 1990-03-14
EP0187702A1 (de) 1986-07-16
ZA8681B (en) 1987-08-26
CA1288774C (en) 1991-09-10
AU5185386A (en) 1986-07-17
JP2546623B2 (ja) 1996-10-23
DE3669503D1 (de) 1990-04-19
JPH0770011A (ja) 1995-03-14
NZ214716A (en) 1989-04-26
JPS61161246A (ja) 1986-07-21
ATE50983T1 (de) 1990-03-15

Similar Documents

Publication Publication Date Title
AU594654B2 (en) 1,2 dialkoxy-omega-trialkylammonium cationic surfactants
US5545412A (en) N-[1, (1-1)-dialkyloxy]-and N-[1, (1-1)-dialkenyloxy]-alk-1-yl-n,n,n-tetrasubstituted ammonium lipids and uses therefor
US4897355A (en) N[ω,(ω-1)-dialkyloxy]- and N-[ω,(ω-1)-dialkenyloxy]-alk-1-yl-N,N,N-tetrasubstituted ammonium lipids and uses therefor
US5208036A (en) N-(ω, (ω-1)-dialkyloxy)- and N-(ω, (ω-1)-dialkenyloxy)-alk-1-yl-N,N,N-tetrasubstituted ammonium lipids and uses therefor
US4946787A (en) N-(ω,(ω-1)-dialkyloxy)- and N-(ω,(ω-1)-dialkenyloxy)-alk-1-yl-N,N,N-tetrasubstituted ammonium lipids and uses therefor
US5049386A (en) N-ω,(ω-1)-dialkyloxy)- and N-(ω,(ω-1)-dialkenyloxy)Alk-1-YL-N,N,N-tetrasubstituted ammonium lipids and uses therefor
DE69800178T2 (de) Glycerolipide verbindungen und ihre anwendung zum transport einer aktiven substanz in eine zielzelle
US5476671A (en) Synthetic ceramides and their use in cosmetic compostions
JP3648686B2 (ja) 脂質小胞の分散物を含有する化粧品学的または製薬学的組成物、その分散物の製造方法並に脂質小胞の分散物
US5824812A (en) Polyfunctional cationic cytofectins, formulations and methods for generating active cytofectin: polynucleotide transfection complexes
AU641886B2 (en) Cosmetic composition
Meekel et al. Synthesis of pyridinium amphiphiles used for transfection and some characteristics of amphiphile/DNA complex formation
JP2018532721A (ja) 治療剤の細胞内送達のための化合物および組成物
US5736395A (en) Amphiphilic imidazolinium derivatives
WO1997021429A1 (en) Radiation-protective phospholipid
AU2022268975A1 (en) Ionizable cationic lipids for rna delivery
DE69301880T2 (de) Amphiphilische fluorierte Schwefel-Polyglycerol Verbindungen, ihre enthaltende kosmetische oder pharmazeutische Zusammensetzungen, Verfahren zu ihrer Herstellung und gestattende Bläschen
DE69531402T2 (de) Kationische transport-reagenzien
US20090232880A1 (en) Analogue Compounds Of Archaebacterial Membrane Lipids And Liposomal Compounds Integrating Such Compounds
WO1999046235A1 (fr) Derives de fullerene
DE69632210T2 (de) Polyfumktionelle kationische cytofectine, formulierungen und verfahren zur herstellung aktiver cytofectin: polynukleotid transfektions-komplexe
EP0188311A2 (de) Pharmazeutische Zusammensetzung von Nicarpidine und 1,2-Dioxy-omega-trialkyl-ammoniumverbindungen
DE69804302T2 (de) Kationische mittel zur transfektion von nukleinsäuren
Hurley et al. Mono-and dicationic short PEG and methylene dioxyalkylglycerols for use in synthetic gene delivery systems
US20230295081A1 (en) Ionizable cationic lipids for rna delivery